9-Methyl-2,3,4,9-tetra­hydro-1H-carbazol-1-one

Thiruvalluvar, A.; Gunaseelan, A.T.; Martin, A.E.; Prasad, K.J.R.; Butcher, R.J.

doi:10.1107/S1600536807034307

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9-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

A. Thiruvalluvar, A. T. Gunaseelan, A. E. Martin, K. J. R. Prasad and R. J. Butcher

The carbazole unit of the title molecule, C₁₃H₁₃NO, is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclohexene ring is in an envelope form. There is an intramolecular C—H

O hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034307/ww2091sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034307/ww2091Isup2.hkl Contains datablock I

CCDC reference: 657788

checkCIF report

Key indicators

Single-crystal X-ray study
T = 203 K
Mean (C-C) = 0.003 Å
R factor = 0.044
wR factor = 0.106
Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.798     1.000
            Tmin(prime) and Tmax expected:      0.967     0.977
            RR(prime) =      0.806
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.98

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           30.51
           From the CIF: _reflns_number_total               1464
           From the CIF: _diffrn_reflns_limit_ max hkl   10.   19.   12.
           From the CIF: _diffrn_reflns_limit_ min hkl    0.    0.    0.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   10.   21.   12.
           Calculated minimum hkl  -10.  -21.  -12.
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.51
           From the CIF: _reflns_number_total               1464
           Count of symmetry unique reflns         1628
           Completeness (_total/calc)             89.93%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Indole and its various substituted products have long been known for their interesting chemical and biological activities (Chandrakantha et al., 1992). The indole ring system is present in a number of natural products, many of which are found to possess pharmacological properties like anti-microbial, anti-inflammatory and anti-implantation activities (Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001). Carbazoles formed by the fusion of indole ring with aromatic six-membered ring, are also widely used in many areas in biological sciences. The structures of these derivatives are analogous to that of ellipticine, a plant alkaloid having pronounced anti-tumour activity and are found to have DNA intercalating properties (Courseille et al., 1974). Synthetic approaches to substituted carbazoles are of special interest and contemporary importance since the growing variety of carbazole alkaloids isolated show anti-microbial, anti-viral (Tubingensin A) and cytotoxic properties (Tubingensin B: a cytotoxic Carbazole alkaloid) against consumption of the sclerotia by insects (Govindasamy et al., 2003). Benzo- and pyrido-annulated carbazoles are pharmacologically interesting since such compounds have potential for the development of compounds with anti-tumor activity. From the above findings it is concluded that the title compound can act as an important synthon to derive such active carbazoles.

Gunaseelan et al. (2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The carbazole unit is not planar. The dihedral angle between the benzene ring and the fused pyrrole ring is 2.5 (1)°. The cyclohexene ring is in envelope form. There is an intramolecular C9—H9A···O1 hydrogen bond.

Related literature top

Several authors (Chandrakantha et al., 1992; Rodriguez et al., 1985; Ebenezer Martin & Rajendra Prasad, 2006; Balamurali & Rajendra Prasad, 2001; Courseille et al., 1974; Govindasamy et al., 2003; Gunaseelan et al., 2007a,b) have reported crystal structures of substituted carbazole derivatives, wherein the carbazole units are not planar.

Experimental top

The mixture of 2,3,4,9-tetrahydro-1H-carbazol-1-one (185 mg, 0.001 mol), methyl iodide (1 ml) and ignited potassium carbonate (276 mg, 0.002 mol) in dry acetone (20 ml) was refluxed on a steam bath for 3 h. The reaction was monitored by TLC. After completion of the reaction, the solvent was removed by distillation and the mixture was poured into crushed ice. The solid obtained was filtered, washed with water and dried. It was purified by column chromatography over silica gel (60–120 mesh) using petroleum ether/ethyl acetate (98:2) as eluant to get the pure title compound (106 mg, 54%). It was recrystallized from petroleum ether/ethylacetate (90:10).

Structure description top

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level. Only one component of the disordered methyl group was shown.

9-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one top

Crystal data top

C₁₃H₁₃NO	D_x = 1.312 Mg m⁻³
M_r = 199.24	Melting point: 453(1) K
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2548 reflections
a = 7.4974 (5) Å	θ = 4.7–30.4°
b = 14.9690 (11) Å	µ = 0.08 mm⁻¹
c = 8.9885 (10) Å	T = 203 K
V = 1008.77 (15) Å³	Block, light-brown
Z = 4	0.39 × 0.37 × 0.28 mm
F(000) = 424

Data collection top

Oxford Diffraction Gemini diffractometer	1464 independent reflections
Radiation source: fine-focus sealed tube	1056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 10.5081 pixels mm^-1	θ_max = 30.5°, θ_min = 5.3°
φ and ω scans	h = 0→10
Absorption correction: multi-scan (CrysAlis CCD or RED?; Oxford Diffraction, 2007)	k = 0→19
T_min = 0.798, T_max = 1.000	l = 0→12
4884 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0626P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1464 reflections	Δρ_max = 0.21 e Å⁻³
136 parameters	Δρ_min = −0.30 e Å⁻³
1 restraint	Absolute structure: see Refinement section in supplementary materials
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₃H₁₃NO	V = 1008.77 (15) Å³
M_r = 199.24	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.4974 (5) Å	µ = 0.08 mm⁻¹
b = 14.9690 (11) Å	T = 203 K
c = 8.9885 (10) Å	0.39 × 0.37 × 0.28 mm

Data collection top

Oxford Diffraction Gemini diffractometer	1464 independent reflections
Absorption correction: multi-scan (CrysAlis CCD or RED?; Oxford Diffraction, 2007)	1056 reflections with I > 2σ(I)
T_min = 0.798, T_max = 1.000	R_int = 0.052
4884 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	Δρ_max = 0.21 e Å⁻³
1464 reflections	Δρ_min = −0.30 e Å⁻³
136 parameters	Absolute structure: see Refinement section in supplementary materials

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N9	0.2382 (2)	0.25379 (10)	0.0201 (2)	0.0289 (4)
C4B	0.2697 (2)	0.39912 (14)	−0.0453 (3)	0.0260 (5)
C4A	0.1978 (3)	0.39569 (13)	0.1011 (3)	0.0250 (5)
C9A	0.1816 (3)	0.30606 (12)	0.1380 (3)	0.0259 (5)
C5	0.3245 (3)	0.46894 (13)	−0.1400 (3)	0.0308 (6)
H5	0.3115	0.5289	−0.1109	0.037*
C8A	0.2933 (3)	0.30931 (14)	−0.0925 (3)	0.0283 (5)
O1	0.1064 (2)	0.19597 (10)	0.3163 (2)	0.0496 (5)
C1	0.1188 (3)	0.27520 (13)	0.2818 (3)	0.0310 (5)
C4	0.1455 (3)	0.46920 (13)	0.2044 (3)	0.0300 (6)
H4A	0.0222	0.4874	0.1846	0.036*
H4B	0.2231	0.5211	0.1888	0.036*
C8	0.3655 (3)	0.28846 (14)	−0.2314 (3)	0.0358 (6)
H8	0.3780	0.2288	−0.2625	0.043*
C7	0.4178 (3)	0.35812 (15)	−0.3211 (3)	0.0389 (6)
H7	0.4681	0.3457	−0.4147	0.047*
C6	0.3975 (3)	0.44756 (15)	−0.2758 (3)	0.0370 (6)
H6	0.4346	0.4937	−0.3397	0.044*
C9	0.2415 (3)	0.15656 (12)	0.0102 (4)	0.0390 (6)
H9A	0.1977	0.1312	0.1026	0.058*	0.50
H9B	0.3628	0.1366	−0.0070	0.058*	0.50
H9C	0.1662	0.1373	−0.0714	0.058*	0.50
H9D	0.2867	0.1388	−0.0865	0.058*	0.50
H9E	0.1216	0.1334	0.0231	0.058*	0.50
H9F	0.3183	0.1327	0.0875	0.058*	0.50
C2	0.0641 (3)	0.34836 (14)	0.3883 (3)	0.0376 (6)
H2A	0.0856	0.3279	0.4903	0.045*
H2B	−0.0643	0.3589	0.3777	0.045*
C3	0.1626 (3)	0.43645 (15)	0.3643 (3)	0.0384 (6)
H3A	0.1139	0.4817	0.4318	0.046*
H3B	0.2890	0.4284	0.3885	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0612 (10)	0.0345 (8)	0.0532 (13)	−0.0010 (7)	0.0077 (11)	0.0149 (8)
N9	0.0321 (8)	0.0220 (7)	0.0327 (9)	−0.0002 (7)	−0.0026 (8)	0.0005 (9)
C1	0.0236 (9)	0.0336 (11)	0.0358 (15)	−0.0005 (8)	−0.0037 (10)	0.0056 (9)
C2	0.0394 (11)	0.0390 (11)	0.0345 (14)	−0.0025 (9)	0.0046 (11)	0.0026 (10)
C3	0.0478 (12)	0.0348 (12)	0.0327 (15)	−0.0042 (10)	−0.0016 (12)	−0.0029 (10)
C4	0.0314 (10)	0.0261 (10)	0.0326 (16)	−0.0001 (7)	0.0009 (11)	−0.0024 (9)
C4A	0.0230 (9)	0.0243 (9)	0.0277 (13)	0.0002 (8)	−0.0048 (10)	0.0011 (9)
C4B	0.0223 (8)	0.0253 (10)	0.0304 (12)	0.0017 (7)	−0.0043 (10)	0.0019 (9)
C5	0.0274 (9)	0.0273 (10)	0.0377 (16)	0.0027 (8)	−0.0016 (11)	0.0077 (10)
C6	0.0334 (10)	0.0410 (11)	0.0366 (16)	0.0035 (9)	0.0007 (12)	0.0140 (11)
C7	0.0355 (12)	0.0545 (14)	0.0267 (13)	0.0091 (9)	0.0027 (11)	0.0002 (11)
C8	0.0345 (10)	0.0374 (12)	0.0355 (16)	0.0041 (9)	−0.0041 (11)	−0.0101 (11)
C8A	0.0243 (9)	0.0283 (10)	0.0321 (15)	0.0018 (8)	−0.0059 (10)	−0.0016 (9)
C9	0.0431 (11)	0.0213 (9)	0.0526 (16)	0.0018 (9)	−0.0100 (12)	−0.0033 (11)
C9A	0.0219 (9)	0.0274 (10)	0.0285 (14)	0.0003 (8)	−0.0045 (9)	0.0013 (9)

Geometric parameters (Å, º) top

O1—C1	1.229 (3)	C2—H2A	0.9800
N9—C8A	1.373 (3)	C2—H2B	0.9800
N9—C9	1.458 (2)	C3—H3A	0.9800
N9—C9A	1.384 (3)	C3—H3B	0.9800
C1—C2	1.511 (3)	C4—H4A	0.9800
C1—C9A	1.451 (4)	C4—H4B	0.9800
C2—C3	1.527 (3)	C5—H5	0.9400
C3—C4	1.524 (4)	C6—H6	0.9400
C4—C4A	1.492 (3)	C7—H7	0.9400
C4A—C4B	1.423 (4)	C8—H8	0.9400
C4A—C9A	1.387 (3)	C9—H9A	0.9700
C4B—C5	1.409 (3)	C9—H9B	0.9700
C4B—C8A	1.421 (3)	C9—H9C	0.9700
C5—C6	1.376 (4)	C9—H9D	0.9700
C6—C7	1.408 (3)	C9—H9E	0.9700
C7—C8	1.375 (3)	C9—H9F	0.9700
C8—C8A	1.396 (4)

O1···N9	2.969 (3)	H3A···H9D^v	2.4700
O1···C9	2.991 (4)	H3B···C7^x	2.9800
O1···H9A	2.2600	H3B···C9A	3.0100
O1···H9E	2.8000	H3B···H7^x	2.5400
O1···H9F	2.7700	H4A···H3A^xii	2.5300
O1···H5ⁱ	2.6600	H4A···H9F^iv	2.5200
O1···H2Bⁱⁱ	2.6600	H4B···C6^xiii	2.9000
O1···H7ⁱⁱⁱ	2.7000	H4B···H6^xiii	2.5900
N9···O1	2.969 (3)	H5···H2B^xii	2.5000
C8A···C9ⁱⁱ	3.522 (3)	H5···O1^vi	2.6600
C9···O1	2.991 (4)	H6···H4B^vii	2.5900
C9···C9Aⁱⁱ	3.538 (3)	H6···C9^vi	3.0800
C9···C8A^iv	3.522 (3)	H6···H9A^vi	2.3400
C9A···C9^iv	3.538 (3)	H6···H9E^vi	2.4700
C1···H9A	2.7600	H7···H3B^viii	2.5400
C3···H9D^v	3.0900	H7···O1^xiv	2.7000
C4···H9F^iv	3.0700	H8···C9	2.8700
C4A···H9B^iv	2.7400	H8···H9D	2.1900
C4A···H9F^iv	2.8800	H9A···O1	2.2600
C4B···H9Eⁱⁱ	2.7500	H9A···C1	2.7600
C4B···H9Cⁱⁱ	3.0300	H9A···C6ⁱ	3.0400
C5···H9Cⁱⁱ	3.0800	H9A···H6ⁱ	2.3400
C5···H9Eⁱⁱ	3.0800	H9B···C8	3.0400
C6···H9A^vi	3.0400	H9B···H3A^ix	2.3900
C6···H4B^vii	2.9000	H9B···C4Aⁱⁱ	2.7400
C6···H9Cⁱⁱ	3.0100	H9B···C9Aⁱⁱ	2.8500
C7···H3B^viii	2.9800	H9C···C8	3.0700
C7···H9Cⁱⁱ	2.9200	H9C···C4B^iv	3.0300
C7···H2A^viii	3.0500	H9C···C5^iv	3.0800
C8···H9Cⁱⁱ	2.9000	H9C···C6^iv	3.0100
C8···H9C	3.0700	H9C···C7^iv	2.9200
C8···H9D	2.6600	H9C···C8^iv	2.9000
C8···H9B	3.0400	H9C···C8A^iv	2.9100
C8A···H9Eⁱⁱ	2.8100	H9D···C8	2.6600
C8A···H9Cⁱⁱ	2.9100	H9D···H8	2.1900
C9···H6ⁱ	3.0800	H9D···C3^ix	3.0900
C9···H3A^ix	2.9200	H9D···H3A^ix	2.4700
C9···H8	2.8700	H9E···O1	2.8000
C9A···H3B	3.0100	H9E···H6ⁱ	2.4700
C9A···H9B^iv	2.8500	H9E···C4B^iv	2.7500
C9A···H9F^iv	2.9100	H9E···C5^iv	3.0800
H2A···C7^x	3.0500	H9E···C8A^iv	2.8100
H2B···H5^xi	2.5000	H9F···O1	2.7700
H2B···O1^iv	2.6600	H9F···C4ⁱⁱ	3.0700
H3A···H4A^xi	2.5300	H9F···C4Aⁱⁱ	2.8800
H3A···C9^v	2.9200	H9F···C9Aⁱⁱ	2.9100
H3A···H9B^v	2.3900	H9F···H4Aⁱⁱ	2.5200

C8A—N9—C9	123.7 (2)	C3—C4—H4A	110.00
C8A—N9—C9A	108.33 (16)	C3—C4—H4B	110.00
C9—N9—C9A	128.0 (2)	C4A—C4—H4A	110.00
O1—C1—C2	121.3 (2)	C4A—C4—H4B	110.00
O1—C1—C9A	123.8 (2)	H4A—C4—H4B	108.00
C2—C1—C9A	114.93 (18)	C4B—C5—H5	121.00
C1—C2—C3	113.9 (2)	C6—C5—H5	121.00
C2—C3—C4	111.7 (2)	C5—C6—H6	119.00
C3—C4—C4A	109.12 (18)	C7—C6—H6	119.00
C4—C4A—C4B	130.42 (19)	C6—C7—H7	119.00
C4—C4A—C9A	122.8 (2)	C8—C7—H7	119.00
C4B—C4A—C9A	106.8 (2)	C7—C8—H8	121.00
C4A—C4B—C5	134.1 (2)	C8A—C8—H8	121.00
C4A—C4B—C8A	106.8 (2)	N9—C9—H9A	109.00
C5—C4B—C8A	119.0 (2)	N9—C9—H9B	109.00
C4B—C5—C6	118.7 (2)	N9—C9—H9C	109.00
C5—C6—C7	121.4 (2)	N9—C9—H9D	109.00
C6—C7—C8	121.4 (2)	N9—C9—H9E	109.00
C7—C8—C8A	117.7 (2)	N9—C9—H9F	109.00
N9—C8A—C4B	108.4 (2)	H9A—C9—H9B	109.00
N9—C8A—C8	129.8 (2)	H9A—C9—H9C	109.00
C4B—C8A—C8	121.8 (2)	H9A—C9—H9D	141.00
N9—C9A—C1	126.99 (17)	H9A—C9—H9E	56.00
N9—C9A—C4A	109.7 (2)	H9A—C9—H9F	56.00
C1—C9A—C4A	123.3 (2)	H9B—C9—H9C	109.00
C1—C2—H2A	109.00	H9B—C9—H9D	56.00
C1—C2—H2B	109.00	H9B—C9—H9E	141.00
C3—C2—H2A	109.00	H9B—C9—H9F	56.00
C3—C2—H2B	109.00	H9C—C9—H9D	56.00
H2A—C2—H2B	108.00	H9C—C9—H9E	56.00
C2—C3—H3A	109.00	H9C—C9—H9F	141.00
C2—C3—H3B	109.00	H9D—C9—H9E	109.00
C4—C3—H3A	109.00	H9D—C9—H9F	109.00
C4—C3—H3B	109.00	H9E—C9—H9F	109.00
H3A—C3—H3B	108.00

C9—N9—C8A—C4B	179.30 (19)	C4—C4A—C4B—C8A	−179.6 (2)
C9—N9—C8A—C8	−2.2 (4)	C9A—C4A—C4B—C5	−176.2 (2)
C9A—N9—C8A—C4B	−0.4 (2)	C9A—C4A—C4B—C8A	0.5 (2)
C9A—N9—C8A—C8	178.1 (2)	C4—C4A—C9A—N9	179.3 (2)
C8A—N9—C9A—C1	−177.6 (2)	C4—C4A—C9A—C1	−2.4 (4)
C8A—N9—C9A—C4A	0.7 (3)	C4B—C4A—C9A—N9	−0.7 (3)
C9—N9—C9A—C1	2.7 (4)	C4B—C4A—C9A—C1	177.6 (2)
C9—N9—C9A—C4A	−179.0 (2)	C4A—C4B—C5—C6	176.9 (2)
O1—C1—C2—C3	152.8 (2)	C8A—C4B—C5—C6	0.6 (3)
C9A—C1—C2—C3	−28.5 (3)	C4A—C4B—C8A—N9	0.0 (2)
O1—C1—C9A—N9	−0.9 (4)	C4A—C4B—C8A—C8	−178.7 (2)
O1—C1—C9A—C4A	−178.9 (2)	C5—C4B—C8A—N9	177.21 (18)
C2—C1—C9A—N9	−179.5 (2)	C5—C4B—C8A—C8	−1.5 (3)
C2—C1—C9A—C4A	2.4 (3)	C4B—C5—C6—C7	0.1 (3)
C1—C2—C3—C4	54.6 (3)	C5—C6—C7—C8	0.0 (4)
C2—C3—C4—C4A	−51.8 (2)	C6—C7—C8—C8A	−0.8 (3)
C3—C4—C4A—C4B	−152.8 (2)	C7—C8—C8A—N9	−176.8 (2)
C3—C4—C4A—C9A	27.2 (3)	C7—C8—C8A—C4B	1.5 (3)
C4—C4A—C4B—C5	3.8 (4)

Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) x+1/2, −y+1/2, z; (iii) x−1/2, −y+1/2, z+1; (iv) x−1/2, −y+1/2, z; (v) −x+1/2, y+1/2, z+1/2; (vi) −x+1/2, y+1/2, z−1/2; (vii) −x+1, −y+1, z−1/2; (viii) x, y, z−1; (ix) −x+1/2, y−1/2, z−1/2; (x) x, y, z+1; (xi) −x, −y+1, z+1/2; (xii) −x, −y+1, z−1/2; (xiii) −x+1, −y+1, z+1/2; (xiv) x+1/2, −y+1/2, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.97	2.26	2.991 (4)	131

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO
M_r	199.24
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	203
a, b, c (Å)	7.4974 (5), 14.9690 (11), 8.9885 (10)
V (Å³)	1008.77 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.39 × 0.37 × 0.28

Data collection
Diffractometer	Oxford Diffraction Gemini
Absorption correction	Multi-scan (CrysAlis CCD or RED?; Oxford Diffraction, 2007)
T_min, T_max	0.798, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4884, 1464, 1056
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.106, 1.02
No. of reflections	1464
No. of parameters	136
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.30
Absolute structure	See Refinement section in supplementary materials

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.9700	2.2600	2.991 (4)	131.00

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